Bickford began racing Quarter Midgets at the age of five, with his father Tom Bickford — who had previously manufactured Quarter Midget parts for Jeff Gordon's father John in the 1970s — playing an early role in his development. By age nine Bickford was racing 48 weeks per year. In 2007 alone he won 69 of 75 races entered across just one of the three Quarter Midget divisions in which he competed.
By 2010 Bickford had accumulated 15 Quarter Midget championships: four local track titles, two NorCal championships, four regional championships, two California 500 championships, two Western States Mona championships, and one Dirt Road National championship, alongside close to 200 main event victories.
To fund his move up to Bandolero cars — which required a HANS device and a new car totalling approximately $6,000 — the 11-year-old Bickford organized the Kids Golf Association charity tournament at Vintner's Golf Club in Yountville, California, arranging hole sponsorships and attracting 16 players entirely without parental assistance.
Bickford entered the Bandolero class in 2010. In his first race at Ukiah Speedway he won the trophy dash, and he went on to set a new track record there with a lap of 15.324 seconds. He won six main events in 14 starts and was named Rookie of the Year at Ukiah Speedway.
Before acquiring his own Legends car, Bickford had the opportunity to test Cole Custer's Legends car in Charlotte, North Carolina, where he was struck by the car's demands for precise throttle control and the limited grip of its tyres.
In 2011 Bickford moved to the Legends of the Pacific Series, claiming the Semi-Pro Legends Championship and earning Legends of the Pacific Rookie of the Year honors with a 41-point lead. His 2012 Legends campaign was cut short in August when he broke his arm during a high school football game the day before he was scheduled to be fitted for a seat in a late model car, though he continued attending the final five races that season without driving.
In 2013 Bickford graduated to full-size race cars as a rookie in the NASCAR Whelen All-American Late Model Series. He won his first career NASCAR feature on May 11, then claimed the championship at All-American Speedway in Roseville, California, becoming the youngest driver in the track's 58-year history to win both a race and the Late Model Series title. He reflected: "I feel like I'm on top of the world. I came into this season just looking to get some practice, but I never imagined winning the championship."
Bickford signed a two-year contract with car owner Bob Bruncati to contest the 2014 NASCAR K&N Pro Series West in the No. 6 Sunrise Ford/Interstate Plastics Ford Fusion, replacing 2013 champion Derek Thorn. Bruncati declared him "the best young driver I've seen in years."
He received personal guidance from cousin Jeff Gordon ahead of his first road course appearance at the 1.99-mile Sonoma Raceway, Gordon walking him through braking, acceleration, and passing points at a circuit where Gordon held five NASCAR Cup victories.
Bickford claimed the 2014 K&N Pro Series West Rookie of the Year title in mid-September after placing third at the Utah Grand Prix, opening a 32-point cushion over Rich DeLong III with two races to go. He became the third consecutive — and fifth overall — Bruncati driver to earn Rookie of the Year honors. Bickford finished fifth overall in the standings with one victory, eight top-five finishes, and nine top-twelve finishes, collecting more points than any other regular series competitor. He was recognised at the NASCAR awards ceremony on December 13 at the NASCAR Hall of Fame in Charlotte.
In 2015 Bickford was invited to join NASCAR Next, NASCAR's elite development program, announced at a ceremony at the NASCAR Hall of Fame. He finished the season eighth in the K&N West standings with 446 points.
In 2018 Bickford returned to competition in the Pacific Coast Challenge Series, driving for Scott Family Racing.
Bickford's career combined extraordinary early achievement — close to 200 Quarter Midget victories and 15 championships by age 11 — with a mature approach to NASCAR junior categories and an aptitude for the business of racing demonstrated by his self-organised junior fundraiser. His family connection to Jeff Gordon added a notable dimension to a career built primarily on his own competitive record.
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